Pyrrole → 1-(3,5-dimethylphenyl)pyrrole

HRID 1242973Notes

Reaction equation

HRID 1242973 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.I[C:7]1[CH:8]=[C:9]([CH3:14])[CH:10]=[C:11]([CH3:13])[CH:12]=1>CCCCCC.C(OCC)(=O)C>[CH3:14][C:9]1[CH:8]=[C:7]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[CH:12]=[C:11]([CH3:13])[CH:10]=1

Participants

4

Reactant 2

HCID 8027PyrroleHCID 1409241-Iodo-3,5-dimethylbenzene

Product 1

HCID 47150831-(3,5-dimethylphenyl)pyrroleYield 99%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Using general procedure B, pyrrole (83 μL, 1.2 mmol) was coupled with 5-iodo-m-xylene to give the crude product. Column chromatography (2×15 cm, hexane:ethyl acetate 9:1) provided 0.170 g (99% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.07 (t, J=7.0 Hz, 2H), 7.02 (s, 2H), 6.89 (s, 1H), 6.33 (t, J=7.0 Hz, 2H), 2.37 (s, 6H).

Workup

  1. customto give the crude product

Sources & evidence

ORD record
ord-efe1f58acf634e75881eb173f6537802
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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